The present invention relates to the field of fragrance compounds and compositions. In particular, the invention concerns the method of production of fragrance compositions as well as their use as, e.g., perfuming, personal care and consumer product ingredients.
5-epi-β-vetivone, represented by Formula (1) below:
is a potentially valuable fragrance component or perfuming ingredient due to its vetivert, woody, grapefruit aroma. Similarly, the mixture of 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one, represented by Formula (3) below
and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one, represented by Formula (4) below
is a potentially valuable fragrance component as well, due to its vetivert, woody, grapefruit aroma.
One method of producing 5-epi-β-vetivone has been developed to date (11). In this process 5-epi-β-vetivone was made as a byproduct during the diastereoselective 1,4-addition of a methyl group to a double bond to synthesize (−)-solavetivone (5). However, 5-epi-β-vetivone is made as a byproduct and the disclosed process is not suitable for commercial grade production of 5-epi-β-vetivone.
No methods of producing 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one (3) and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one (4) are known to date.
Therefore, there is a current need in the art for methods to produce 5-epi-β-vetivone (1) in a fewer number of reaction steps, with higher overall yield, and from less expensive and more available starting materials. Furthermore, there is a current need in the art for methods to produce 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one (3) and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one (4).
Accordingly, the present invention is directed to novel methods for production of 5-epi-β-vetivone, 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one (3) and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one (4), which are useful for their fragrant qualities. The production of the fragrance compositions as described by the present invention can be used for the preparation of perfumes, household products, laundry products, body care products or cosmetic products, as well as related compositions and articles. Mixtures of the compound described in the invention, a fragrance modifying composition, a perfume composition and a cologne composition are also included in the invention. The compounds and compositions can be employed in order to confer a woody, grapefruit, or vetivert odor to a variety of products.